Sneak Thief Extraordinaire and its preceding achievements are awarded for successfully picking many citizens' pockets. The Light Fingers skill will help considerably. Khajiit will also have a bit of an edge on this one. Even so, expect to be caught a fair amount, especially early on before you acquire enough points in the skills that help you to avoid detection. The second and third achievements will allow you to purchase Pocket Change and Noble Pocket Lint for your home. They cost 00000500500 and 000010001,000 , respectively and can be purchased from any Outlaws Refuge Merchant.